The fact that the head of the CIA is in Havana meeting with senior government figures suggests that things could be about to move — and possibly break — very quickly.
Almost exactly 65 years after the Bay of Pigs debacle, the US is reportedly considering another military invasion of Cuba. President Trump has repeatedly mused about taking over Cuba, as his administration tightens its starvation siege of the island nation. Last Friday, he even suggested that an aircraft carrier returning to the US from Iran could be stationed offshore.
This, of course, presupposes that US aircraft carriers will be returning from the Persian Gulf any time soon, which perhaps smacks of wishful thinking. One thing that is apparently happening is that the US Air Force is intensifying its reconnaissance flights off Cuba’s coast, just as it did before the January 3 attack against Venezuela, reports Drop Site News:
The U.S. Navy and Air Force have conducted at least 25 intelligence-gathering flights off the coast of Cuba since February 4, most of them near Havana and Santiago de Cuba and some coming within 40 miles of the coast, a CNN analysis of publicly available aviation data showed—a sudden surge with no precedent in recent years.
The aircraft involved include P-8A Poseidon maritime patrol planes, RC-135V Rivet Joint signals intelligence aircraft, and MQ-4C Triton high-altitude drones—the same platforms that conducted surveillance ahead of U.S. special forces’ capture of Venezuelan President Nicolás Maduro and ahead of joint U.S.-Israeli strikes on Iran.
CNN noted that a similar pattern of escalating rhetoric coinciding with a visible uptick in surveillance flights preceded both of those operations, and that the aircraft are capable of masking their location beacons but have not done so, raising the question of whether the flights constitute a deliberate signal to Havana.
This intensification of military activity around Cuba coincides with the collapse of the Cuban economy brought about by the US’ near-total energy blockade. Since January, neither Venezuela or Mexico, the island’s two biggest energy providers have been able to send oil. The delivery of 730,000 barrels of crude oil by the Russian-flagged Anatoly Kolodkin in late March brought a brief respite, but that oil has been used up and there are no signs of replenishments.
🇨🇺 BREAKING: Cuba is completely out of diesel and fuel oil
Cuba has completely exhausted its diesel and fuel oil reserves, Energy Minister Vicente de la O Levy announced Wednesday on state media, prompting protests across the capital on Wednesday evening.
Some districts in the… https://t.co/VhA7UiM8XR
— Drop Site (@DropSiteNews) May 14, 2026
“We are going to continue providing support to Cuba,” said the Russian ambassador in Havana, Víctor Koronelli. However, support from other countries is desperately needed, he added: “It would be very important for other countries, countries that are friends of Cuba, to try to break this energy siege as Russia did. If we act in this way, united, that will yield results.”
But time is running out. By Wednesday, Cuba had completely exhausted its diesel and fuel oil reserves. As the nationwide blackouts drag on for up to 20-22 hours per day in Havana (imagine what the countryside has like, protests have begun to break out as some of Cuba’s long-suffering residents lose their patience. From yesterday’s Financial Times:
Protests erupted overnight in Cuba after the government said it had completely run out of diesel and fuel oil, the energy supplies essential to its power generation.
Energy minister Vicente de la O Levy blamed US President Donald Trump’s near-total energy blockade of the communist island over the past four months for the crisis.
“We have absolutely no fuel [oil] and absolutely no diesel,” he said on Wednesday in remarks carried on state-run media. “We have no reserves.”
Cuba’s President Miguel Díaz-Canel called the country’s energy situation “particularly tense”, writing in a post on X that he blamed the “dramatic worsening” on the “genocidal US blockade”.
Images shared on social media showed protests had broken out overnight in parts of the capital, Havana, with residents banging pots and pans and burning blockades in the streets. There were reports of clashes with police.
Havana’s long reliance on Venezuelan oil supplies — which it traded for Cuban doctors and spies — was severed in January when US troops snatched hardline leader Nicolás Maduro.
Mexico delivered one oil cargo to Cuba on January 9 but then, under pressure from Trump, also halted shipments. In late January, Trump threatened tariffs on any country that supplied Cuba as the administration in Washington ratchets up pressure to try to bring about regime change.
My first assumption on hearing this news was that CIA assets would be well represented at said protests. Hours later, the following news alert appeared on my Twitter feed:
Cuba says CIA Director John Ratcliffe quietly met with officials in Havana, as it deals with an energy sector collapse and rising tensions with the US.https://t.co/b4FuzpMgPL
— CNN (@CNN) May 14, 2026
So, for the first time ever, a CIA director is meeting with senior representatives of Cuba’s communist government — something that would have been unimaginable just months ago. From the CNN article:
CIA Director John Ratcliffe led a US delegation to Havana to meet with Cuban government officials on Thursday as the island deals with a collapse of its energy sector amid rising tensions with the US, according to the Cuban government.
“Following the request submitted by the US government that a delegation presided over by the CIA Director John Ratcliffe be received in Havana, the Revolutionary Directorate approved the realization of this visit and the meeting with its counterpart from the Ministry of the Interior,” the statement read.
Havana said its officials stressed in the meeting that Cuba “does not constitute a threat to the national security of the US” and that there are no “legitimate reasons” to include it on the US’s list of State Sponsors of Terrorism, as it has been under the Trump administration. They also insisted the country does not harbor, support or fund terrorists – something the US has long accused it of doing – and denied hosting foreign military or intelligence bases.
The energy blockade is just one aspect of the Trump administration’s total economic siege against Cuba. The targets of that siege have even included the island’s international medical missions. As we reported in a previous post, this measure has not only deprived Havana of one of its most important sources of foreign currency; it has also deprived dozens of countries in the “Global South” of the vital medical care provided by Cuban doctors.
We will probably never know how many people have died, needlessly, as a result of these sanctions. According to a paper published last year in Lancet (which we covered here), US-led sanctions have led to around 564,000 deaths annually since 1970 — a mortality burden similar to or even higher than total direct deaths from armed conflicts.
In the clip below, Cuba’s Foreign Minister Bruno Eduardo Rodríguez Parrilla describes the US blockade as “an act of genocide and collective punishment”. Infant mortality, he says, has doubled, and 12,000 children are awaiting surgery.
🇨🇺 Canciller cubano:
“Es un acto de genocidio y castigo colectivo… la mortalidad infantil se ha duplicado, 12.000 niños esperan cirugías… la asfixia total siempre ha sido el verdadero objetivo de la política de EE.UU. hacia Cuba.” pic.twitter.com/xjCud7D6wW— Tere Felipe (@_TereFelipe_) May 14, 2026
“From 2018 to 2025, as U.S. sanctions grew more punitive, Cuba’s once-impressive infant mortality rate skyrocketed by 148 percent,” @RepJayapal and @rep_jackson write in @nytopinion, citing a recently released CEPR report. pic.twitter.com/5oWf3uVcQF
— CEPR (@ceprdc) May 12, 2026
As Fidel Castro once said, one of the reasons why Washington so despises Cuba is that it constantly casts the US model in a bad light. The fact that Cuba has (or at least had until Washington escalated its siege) similar life expectancy to the US, lower infant mortality, better primary care coverage (at a fraction of the cost) and a higher literacy rate despite decades of US sanctions is (or at least should be) the ultimate badge of shame for Washington.
Fidel Castro explains why the US despises Cuba and is desperate to destroy it: “Our country does not drop bombs on other people, nor does it send thousands of planes to bomb cities. Instead our country sends doctors to those most lost corners of the world.” pic.twitter.com/qrTUMgWSEC
— ☀️👀 (@zei_squirrel) January 30, 2026
In recent weeks, the US has continued to tighten the screw on Cuba’s suffocating economy. On May 1, the Trump administration authorised sweeping restrictions against any foreign individual or entity that US State Department deems to have operated in priority areas of the Cuban economy.
Days later, US Secretary of State Marco Rubio issued crippling secondary sanctions against Cuba’s military-run business conglomerate GAESA, its director Ania Guilermina Lastres Morera, and a Canadian-Cuban joint mining venture, Moa Nickel SA, which is co-owned by one of Cuba’s largest foreign investors, Sherritt International.
When asked about the sanctions, Rubio claimed that GAESA is “a company that basically is taking anything that makes money in Cuba and illegally putting it into the pockets of a few regime insiders.” However, as Arturo Dominguez notes, Rubio is conveniently ignoring the fact that GAESA, like any large state-owned company, has a huge economic footprint:
“[H]e’s ignoring that millions of Cubans work for state-run companies that operate under GAESA. Like most other unilateral economic sanctions imposed by the United States, these directly impact the Cuban people and result in suffering and death, particularly for the most vulnerable Cubans.
In anticipation of the Treasury Department designation, Sherritt, which also produces Cuban natural gas for electricity generation and is Cuba’s largest foreign investor, announced that its senior leadership had resigned as the company and its employees begin packing their bags after more than three decades of operating in Cuba.
As Lee Schlenker writes for Responsible Statecraft, the third-party sanctions have put foreign hotel operators, financial institutions, and energy companies operating in Cuba — particularly the Spanish hotel chains Meliá and Iberostar, both of which also manage U.S. properties — on high alert:
The administration has only given foreign firms a tight four-week window to wind down transactions with any GAESA-owned entities before their U.S. assets are blocked.
A source with knowledge of companies’ operations tells RS that financial institutions, particularly across Canada, the European Union and Latin America, have initiated a de facto boycott of all transactions involving Cuba given their potential exposure to costly Treasury Department enforcement actions. “Additional designations can be expected in the following days and weeks,” [US Secretary of State Marco] Rubio said Thursday.
As conditions deteriorate in Cuba, Rubio is barely able to contain his glee. Like other Cuban-American politicians, he has built his career on vilifying the Cuban Revolution and trying to economically strangle and starve into submission the people of his parents’ homeland.
“What is happening in Cuba is unacceptable,” said Rubio (in Spanish) while traveling to China aboard Air Force One. “And having a failed state just 90 miles off our coast is a threat to the United States. It is a state that is not functioning worse than ever, with a regime that not only does not allow open political activity but is also economically destroying the lives of Cubans.”
The fact that Rubio can say those last six words with a straight face while imposing the harshest economic siege on his parents’ native country — a siege that is literally killing people right now — is testament to why Rubio is such a dangerous and clearly sociopathic US secretary of state — not only for Cuba but the entire Latin American region, for which he has such apparent disdain.
Rubio even offered Cuba the ultimate insult: $100 million dollar in humanitarian aid, to be distributed through branches of the Catholic Church. That works out at roughly $10 per Cuban man, women and child — an amount that pales in comparison with the amount of damage the US has wrought, not just in recent months but over the course of sixty-six and a half years.
The original intent of US sanctions on Cuba, initiated in the early 1960s by the Kennedy administration, was to economically asphyxiate the Cuban Revolution, punish the Castro government for nationalizing US assets, and provoke enough hunger and desperation to overthrow Fidel Castro’s communist regime.
That goal may soon be in reach, though Fidel has long departed. The fact that the head of the CIA is in Havana meeting with senior government figures, including Raúl Rodríguez Castro, äka “Raulito”, Raúl Castro’s grandson and right-hand man, as well as with the Cuban Minister of the Interior, Lázaro Álvarez Casas, and the head of the Cuban spy services., suggests things could be about to move — and possibly break — very quickly.
The matters under discussion apparently included intelligence cooperation, economic stability, and security, on the basic proviso that Cuba can no longer be a safe haven for adversaries in the Western Hemisphere. Also on the negotiating table were issues such as the release of political prisoners, the installation of Starlink satellite services in Cuba, the possibility of dismantling Cuba’s six-decade economic embargo the need for greater political freedoms.
🇺🇸🇨🇺CIA official: “Today, Director Ratcliffe met with Cuban officials, including Raulito Rodriguez Castro, Minister of Interior Lazaro Alvarez Casas, and the head of Cuban intelligence services in Havana to personally deliver President Trump’s message that the United States is…
— Barak Ravid (@BarakRavid) May 14, 2026
This is all happening just days before Cuban Independence Day (May 20), which marks the end of the US’ de facto occupation of the island in the decades prior to the Cuban Revolution. After his disastrous war of choice in Iran, Trump desperately needs a quick and easy foreign policy win. The question is: will Cuba provide it?
To me, this signals that the Pirate State could be planning another kidnapping operation against Cuba like they did in Venezuela. This is the lawless behavior they want to normalize around the world. https://t.co/RV3JZgBQeQ
— Richard Medhurst (@richimedhurst) May 15, 2026
“There’s definitely a sense of expectation and anxiety in Miami and Cuba”, Sebastian Arcos, Interim Director for the Institute for Cuban Studies at Florida International University, told Axios:
[He] believes intervention was possible shortly after Trump declared Cuba an imminent threat to U.S. security in January, but then the Iran War shifted military assets to the Middle East.
“Everything was put on the back burner. Now that we see that the Iran war is sort of in limbo … I can see a sort of a refocusing on Cuba, not just in the [surveillance] flights, but also the statements from the President to Marco Rubio, and the sanctions that were just announced.”
Arcos added that he doesn’t believe Trump will put boots on the ground, but that he might pursue an “off distance military action” similar to what happened in Iran that will “shock the regime, crack the leadership and perhaps create an opportunity for new leadership to rise.”
What Arcos doesn’t mention is that while new leadership has indeed risen in Iran, its leadership structures are much more dispersed and it is, if anything, even more opposed to US and Israel’s imperial designs on Iran. What could happen if the US were to attack Cuba is difficult to say.
Cuba’s President Miguel Díaz-Canal insists that the people of Cuba are willing and ready to fight off any US invasion, just as Castro’s forces did in the Bay of Pigs debacle. But the Cuba of today has been desperately weakened by the US sanctions and energy blockade, and Díaz Canal does not enjoy the popular support Fidel once commanded. That said, Cuba is not Venezuela.
In an interview with Russian state television Rossiya 24 in February, Russia’s ambassador to the UN, Vasili Nebenzya, said the US would fail to replicate the January 3 coup against Maduro. In the case of Venezuela, he said, there were internal fractures and betrayals in the upper echelons of power that facilitated the coup. By contrast, in the case of Cuba, the political system is more cohesive and monolithic.
Interestingly, the UN Secretary General António Guterres made a similar observation this week, warning that there is no military solution to the current impasse in Cuba and calling for a “constructive dialogue” instead. He also reiterated that the US’ blockade and sanctions on Cuba violate international law:
In Venezuela, honestly, we saw a military operation against Maduro, but I have the impression that there was great complicity within the Venezuelan political system. Therefore, comparing Venezuela with Cuba seems to me an unfair comparison.
One thing that is clear is that any military operation against the Caribbean’s largest island, which is already in the grip of a US-made humanitarian crisis, will create significant destabilisation in the region, including waves of migration to the US. If the war in Iran has taught us anything, it is that Trump 2.0 does not excel when it comes to contingency planning for the second and third order effects of its ill-thought military actions.
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